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I try to keep it simple with 2 cards: An Amazon visa that gives me 5% back on Amazon purchases (which for me is a lot of money on an annual basis) and a Citicard that gives me 2% on everything else. I prefer cash back to “points” because I can use it for anything with no effort. But I am considering a United card that will give me 70,000 bonus miles in anticipation of a big vacation in the next year.
I prefer using a smaller number of zero-fee cards that return cash rewards. I use Costco Citi for gas, Costco purchases, travel and dining; an Amazon Chase Card for Amazon and Whole Foods purchases; and Fidelity Elan for everything else.
For myself, the best strategy is to just hold one ‘all purpose’ rewards card and pay it off every month. I use a Costco Citi card to pay for nearly all of my monthly expenses. I typically get a $250-$300 cash reward in February of each year.